Villa holiday rentals in Bennington

Find and book unique villas on Airbnb

Top-rated villa rentals in Bennington

Guests agree: these villas are highly rated for location, cleanliness and more.

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Guest favourite

Villa in Niskayuna

4.92 out of 5 average rating, 38 reviews

Mansion near Saratoga NY, Hibachi, HotTub, Masseur

30 day, Seasonal Retreat, Top choice for business travelers & Friends/Couples. Perfectly located for Saratoga & Racetrack, Lake George, Albany, boating, ski & all Capital Region adventures. Escape the city & create memories - Experience The Hilltop Mansion at Rebecca's Fountain, in a hidden Estate overlooking the Mohawk River, Marina & Mountains. 11 bed oasis on 3 acres w/ pond, HotTub, outdoor games add extras like Private Hibachi Chef, Catering, Masseur, & more. Staff onsite. Experience more!

The house is set on a grassy lot, featuring a screened porch and large windows. Well-kept shrubs line the property, and mature trees provide shade. The structure's exterior displays a soft neutral tone, with a distinct architectural style that offers charm and character.

Villa in Queensbury

5 out of 5 average rating, 3 reviews

Private City Line Compound

2 Bedroom,s sleep 4, Walk to Coffee Shop, Breakfast, locations, Restaurants, Grocery Market, medical. West Mountain Ski Area 5 miles away. Summer activities there . Bike path to lake George accessibility from house. 2 car secure garage . 6 person Hot Tub on outdoor porch, with 43” TV. 63’ TV in Living , Room, Sonos Theatre sound system 43” TV’s in Bed Rooms . WiFi/internet/cable Outdoor gas grill Breakfast Nook 65" Outdoor TV and seating area All amenities For a vacation stay. No Garage

Guest favourite

A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.

Villa in Winhall

4.89 out of 5 average rating, 27 reviews

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

Guest favourite

A spacious living area features a large sectional sofa positioned around a warming fireplace, with logs neatly stacked beside it. Natural light fills the space through multiple windows, while a spiral staircase leads to the upper level. Soft area rugs add comfort to the wooden floor.

Villa in Dover

4.89 out of 5 average rating, 19 reviews

Huge Stunning Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Welcome to Mt Snow Villas!, Your ultimate mountain experience at Mount Snow. This stunning duplex villa offers a harmonious blend of luxury, comfort, and convenience, making it the perfect choice for large groups, family gatherings, or anyone seeking an unforgettable escape to the mountains. With the indulgence of a Jacuzzi, hot tub, and sauna, your stay promises both relaxation and rejuvenation. ASK US ABOUT RENTING ALL 6 VILLAS AND HOSTING UP TO 60 PEOPLE FOR YOUR NEXT PARTY!

Guest favourite

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

4.94 out of 5 average rating, 90 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

Guest favourite

A spacious dining area features a large wooden table set for eight, complemented by modern gray chairs. Large windows offer views of the wooded surroundings, while a spiral staircase leads to an upper level. A cozy living area is visible in the background.

Villa in Dover

4.8 out of 5 average rating, 20 reviews

Large Updated Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Relax at Mt Snow Villas!! Welcome to our gorgeous mountain villa duplex nestled in the heart of breathtaking West Dover just 1/2 mile from Mount Snow! If you're seeking a peaceful escape from the hustle and bustle of everyday life, this spacious villa offers a perfect blend of warmth, elegance and modern comfort, making it the ideal getaway for couples, families, or groups of friends.

A game room is highlighted by a foosball table and several pool tables. Green pendant lights hang above the pool tables, providing illumination. The floor features wood-like flooring, enhancing the spacious feel of the area. Walls are painted in neutral tones, contributing to a relaxed atmosphere.

Villa in Brownsville

4.79 out of 5 average rating, 72 reviews

Villa with a Fireplace Near the Trails

Dreaming of a cozy villa with a fireplace? You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

An indoor pool area features a long, rectangular swimming pool surrounded by multiple lounge chairs. The high, vaulted ceiling is supported by metal beams, and large windows provide natural light to the space, creating a bright and inviting atmosphere.

Villa in Brownsville

4.8 out of 5 average rating, 10 reviews

Villa Near Biking and Hiking Trails

This villa is perfect for your group! Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

An indoor pool area is highlighted by clear blue water under a high, metallic ceiling. Surrounding the pool, multiple lounge chairs are arranged for relaxation. Large windows provide natural light, creating a bright atmosphere throughout the space.

Villa in Brownsville

4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

An indoor pool area is featured, with a spacious swimming pool lined by blue lounge chairs. Large windows allow natural light to fill the room, enhancing the bright atmosphere. The covered structure showcases a high ceiling, ensuring a comfortable swimming experience year-round.

Villa in Brownsville

4.83 out of 5 average rating, 23 reviews

Villa with Pool + Fitness Center Access

Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Guest favourite

Private room in Troy

5 out of 5 average rating, 18 reviews

Warm & Elegant Suite/Free parking spaces

Cozy Private Suite in Troy, You will have exclusive use of one bedroom and one living room. Enjoy fast Wi-Fi, heating/AC, coffee corner, and free parking. Only 8 min to Downtown Troy, and 12 min to Albany. No smoking, no parties.